Debian stable not booting, freezes

I am attempting to use debian stable as a production server for a
hosting company that is primarily windows based, in a attempt for
them to start supporting the open source community and linux itself,
but am having allot of problems that are only showing the owner that
"windows is in fact the superior operating system, because I would
have had this server up days ago" (his words).
For the past few weeks, we have reloaded the server several times
since for some strange reason any attempt to upgrade the kernel to a
2.4.x release from the default 2.2.X install kernel couses it to
either refuse to boot or if it does boot, freeze up the system.
We need a newer kernel version both for security reasons, and the
fact that the default FD_MAX for the 2.2.x release seems to be 255
and thus we can get apache to load, it errors out with a error saying
it can not open any more files.
I run debian (both stable and unstable) on my private network, and I
have never seen this happen before; Im sick and tired of working on
this same server for the past weeks, and I have used only stable
debian standard packages in the installation, I googled and I still
have no idea what is going on or why.
Has anyone experienced these refusals to boot or the random freezes?
This is the only OS on the computer in question, a 1ghz Intel p3 with
512 ram, and the first boot did so like a dream under the 2.2.x
kernel, but it was simply too old for the needs of the server.
I know I am rambling, sorry about that but I have been up for the
past 2 days trying to figure this out, if you have ANY input at all
please do so, I am stumped and this is really making linux look bad
compared to windows in a server environment, and I think I hate that
most of all.